Water → 1,2-Propanediol, 3-((p-benzyloxy)phenoxy)-

HRID 330498Notes

Reaction equation

HRID 330498 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH2:4][O:3]1.O>C(Cl)Cl>[C:17]1([CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH:5]([OH:6])[CH2:4][OH:3])=[CH:10][CH:11]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 962WaterHCID 133384952,2-Dimethyl-4-[[4-(phenylmethoxy)phenoxy]methyl]-1,3-dioxolane

Product 1

HCID 2310801,2-Propanediol, 3-((p-benzyloxy)phenoxy)-Yield 38.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.98 g of 2,2-dimethyl-4-[[4-(phenylmethoxy)phenoxy]methyl]-1,3-dioxolane, 15 g of a strongly acidic ion exchange resin and 200 ml of water was refluxed for 24 hours, then allowed to cool and methylene chloride was added. The mixture was filtered and the organic layer separated and saved. The aqueous layer was extracted several times with methylene chloride. All organic solutions were combined, dried and evaporated, giving 3.0 g of the desired compound, mp 125°-127° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureto cool
  3. filtrationThe mixture was filtered
  4. customthe organic layer separated
  5. extractionThe aqueous layer was extracted several times with methylene chloride
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-2a0a8a14e4764440bb210a90b3124989
Source dataset
uspto-grants-1990_01
Patent number
US04897385

Reaction notes

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