Chloroacetyl chloride → HCID 86605475, compound

HRID 2103000Notes

Reaction equation

HRID 2103000 reaction equation
[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[C:11]2[C:3]=1[CH2:4][CH2:5][C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].[Cl:20][CH2:21][C:22](Cl)=[O:23]>C(Cl)Cl>[Cl:20][CH2:21][C:22]([O:15][C:14]1[C:2]([CH3:1])=[C:3]2[C:11](=[C:12]([CH3:17])[C:13]=1[CH3:16])[O:10][C:6]1([CH2:7][CH2:8][CH2:9]1)[CH2:5][CH2:4]2)=[O:23]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 11543182HCID 11543182, compound

Product 1

HCID 86605475HCID 86605475, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (500 mg) in anhydrous CH2Cl2 (3 mL) was mixed with a 15% aq. NaOH solution (2.0 mL). The resulting mixture was cooled to 0° C. and stirred vigorously while being treated with slow addition of a solution of chloroacetyl chloride (0.534 mL) in CH2Cl2 (2 mL). The reaction mixture was allowed to warm up to ambient temperature and stirred for an additional 6 h. Upon layer separation, organic phase was collected and dried over Na2SO4, followed by solvent evaporation. Column chromatography (SiO2: hexane:EtOAc, 95:5 v/v) yielded 5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl chloroacetate as a pale yellow solid (204 mg).

Workup

  1. temperatureto warm up to ambient temperature
  2. stirringstirred for an additional 6 h
  3. customUpon layer separation, organic phase
  4. customwas collected
  5. dry with materialdried over Na2SO4
  6. customfollowed by solvent evaporation

Sources & evidence

ORD record
ord-36e67e5d72624bd4b6a7f405158df350
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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