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Lithium Hydroxide → HCID 9866334, compound

HRID 1250094
Notes
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Reaction equation

HRID 1250094 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14](=[O:28])[N:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]=1[Cl:29].[OH-].[Li+]>CO.O.O1CCCC1>[Cl:29][C:7]1[C:8]([CH2:12][O:13][C:14](=[O:28])[N:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:30])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 15550612HCID 15550612, compound

Product 1

HCID 9866334HCID 9866334, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028
Tetrahydrofuran
Solvent

Procedure

{2-Chloro-3-[(diphenylcarbamoyloxy)methyl]phenoxy}acetic acid methyl ester (0.64 g, 1.5 mmol) was dissolved in a mixture of methanol (20 mL), water (5 mL), and tetrahydrofuran (2 mL). An aqueous solution of lithium hydroxide (0.07 g, 1.65 mmol) was added and the mixture was allowed to stir overnight. The mixture was concentrated in vacuo, and the residue diluted with water and washed with diethyl ether. The aqueous layer was acidified with 3M hydrochloric acid forming a white precipitate which was filtered and dried. Recrystallization from methanol gave {2-chloro-3-[(diphenylcarbamoyloxy)methyl]phenoxy}acetic acid as white needles (0.47 g, 76.5%); m.p. 182.2-182.9° C.; 1H NMR 4.66 (s, 2H), 5.30 (s, 2H), 6.83 (dt, J=7.5Hz, 2H), 7.11 (t, J=8.0Hz), 7.28 (m, 10H); 13C NMR 64.98 (t), 66.02 (t), 112.96 (d), 121.62 (d), 126.27 (d), 126.93 (d), 127.02 (d), 128.94 (d), 135.79 (s), 142.34 (s), 153.68 (s), 154.27 (s), 170.26 (s). Analysis for C22H18ClNO5: Calcd.: C, 64.16; H, 4.41; N, 3.40. Found: C, 64.30; H, 4.39; N, 3.56.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with water
  3. washwashed with diethyl ether
  4. filtrationwas filtered
  5. customdried
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-9e15b6c27a52453ea9e98df3f8d13948
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06335459B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes