Methanol → HCID 21074214, compound

HRID 1373183Notes

Reaction equation

HRID 1373183 reaction equation
[O:1]([CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=1)[C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CO>C1COCC1>[O:1]([CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21074225HCID 21074225, compound

Product 1

HCID 21074214HCID 21074214, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3,5-diphenoxymethylbenzoate (525 mg 1.51 mM) 2.0M sodium hydroxide (2.3 n 4.6 mm) methanol (5 ml) water (3 ml) and THF (10 ml) were stirred together at room temperature for 3 hours. After concentrating to ½ volume the mixture was acidified with 2.0M hydrochloric acid and partitioned between ethyl acetate and water. The organic extracts were washed with water, dried (magnesium sulphate) filtered and evaporated to give 3,5-diphenoxymethylbenzoic acid as a colourless solid (500 mg, 99%); H1 NMR δ (d6-DMSO) 5.19 (4 H s) 6.9–7.18 (6 H m) 7.28 (4 H t) 7.78 (1 H s) 7.95 (2 H s); MS [MH]− 333.

Workup

  1. concentrationAfter concentrating
  2. custompartitioned between ethyl acetate and water
  3. washThe organic extracts were washed with water
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1c37e8b3026a48cfaf6dcdde50d5b091
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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